Hydrochloric Acid → HCID 86642978, compound

HRID 888324Notes

Reaction equation

HRID 888324 reaction equation
[C:1]1(C)[CH:6]=CC(S(OCCC#C)(=O)=O)=[CH:3][CH:2]=1.[F:16][C:17]([F:29])([F:28])[CH2:18][CH2:19][S:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])(=[O:22])=[O:21].[H-].[Na+].Cl>CS(C)=O>[F:29][C:17]([F:16])([F:28])[CH2:18][CH2:19][S:20]([CH:23]([CH2:3][CH2:2][C:1]#[CH:6])[C:24]([O:26][CH3:27])=[O:25])(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2720203-Butynyl p-toluenesulfonateHCID 57425720Methyl 2-(3,3,3-trifluoropropylsulfonyl)acetate

Product 1

HCID 86642978HCID 86642978, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2.0 g of 3-butynyl p-toluenesulfonate and 2.1 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 30 ml of dimethyl sulfoxide, 0.4 g of sodium hydride (60% in oil) was added at room temperature, and stirred at the same temperature for 4 days. To the reaction mixture, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.90 g of methyl 2-(3,3,3-trifluoropropylsulfonyl)-5-hexynoate (hereinafter referred to as the present compound (8)).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5d50dcdc9ce4c2687bcc6c359649102
Source dataset
uspto-grants-2012_08
Patent number
US08247595B2

Reaction notes

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